GB1166711A - Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives - Google Patents

Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives

Info

Publication number
GB1166711A
GB1166711A GB03676/66A GB1367666A GB1166711A GB 1166711 A GB1166711 A GB 1166711A GB 03676/66 A GB03676/66 A GB 03676/66A GB 1367666 A GB1367666 A GB 1367666A GB 1166711 A GB1166711 A GB 1166711A
Authority
GB
United Kingdom
Prior art keywords
formula
indane
phenyl
tetralin
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB03676/66A
Inventor
Povl Viggo Petersen
Villy Halfdan Hansen
Jes Hjortkjaer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kefalas AS
Original Assignee
Kefalas AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kefalas AS filed Critical Kefalas AS
Priority to GB03676/66A priority Critical patent/GB1166711A/en
Priority to NL666613828A priority patent/NL146047B/en
Priority to NO00167337A priority patent/NO127052B/no
Priority to DE19671618583 priority patent/DE1618583A1/en
Priority to AT278567A priority patent/AT273947B/en
Priority to SE04105/67A priority patent/SE338564B/xx
Priority to NL6704297A priority patent/NL6704297A/xx
Priority to CH435667A priority patent/CH491076A/en
Priority to DK160967AA priority patent/DK124820B/en
Priority to FI670883A priority patent/FI48458C/en
Publication of GB1166711A publication Critical patent/GB1166711A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Abstract

1,166,711. Phenyl-indane and tetralin derivatives. KEFALAS A/S. 21 March, 1967 [28 March, 1966], No. 13676/66. Heading C2C. Phenyl-indane and tetralin derivatives of the formula wherein R<SP>1</SP> and R<SP>2</SP> each represent hydrogen or a C 1-8 alkyl group; n is 1 or 2; " alkylene " represents a branched or unbranched alkylene chain containing from 3 to 8 carbon atoms, 3 carbon atoms being in the chain directly connecting the ring system with the nitrogen atom; R<SP>3</SP> and R<SP>4</SP> each represent hydrogen or a C 1-8 alkyl or benzyl group, provided that R<SP>3</SP> and R<SP>4</SP> do not both represent hydrogen, or R<SP>3</SP> and R<SP>4</SP>, taken together with the nitrogen atom, represent a heterocyclic amine radical having a saturated 5- or 6-membered ring; and X and Y each represent hydrogen, a halogen, or a C 1-8 alkyl, C 1-8 alkoxy or trihalomethyl group; and non-toxic acid addition salts thereof are prepared by reacting a tertiary alcohol of the formula with a dehydrating agent capable of causing ring formation and isolating the phenyl-indane or tetralin derivative of the first formula above as the free amine or as a non-toxic acid addition salt thereof; and, in the case when R<SP>3</SP> and R<SP>4</SP> each represent a C 1-8 alkyl group, optionally reacting the resulting phenyl-indane or -tetralin derivative of the first formula above with a chloroformic acid ester of the formula Cl.COOR<SP>6</SP>, wherein R<SP>6</SP> represents a C 1-8 alkyl or benzyl group, hydrolysing the resulting ester of the formula and isolating the phenyl-indane or -tetralin derivative of the first formula above wherein R<SP>3</SP> is a C 1-8 alkyl group and R<SP>4</SP> is hydrogen as the free amine or as a non-toxic acid addition salt thereof. Tertiary alcohols of the second formula above are prepared by reacting a ketone of the formula with a Grignard reagent of the formula hal. Mg.alkylene.NR<SP>3</SP>R<SP>4</SP>, wherein hal is a chlorine, bromine or iodine atom, and hydrolysing the intermediate thus formed.
GB03676/66A 1965-10-01 1966-03-28 Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives Expired GB1166711A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB03676/66A GB1166711A (en) 1966-03-28 1966-03-28 Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives
NL666613828A NL146047B (en) 1965-10-01 1966-09-30 PROCESS FOR THE PREPARATION OF A PHARMACEUTICAL PREPARATION WITH PSYCHOTHERAPEUTIC ACTION.
NO00167337A NO127052B (en) 1966-03-28 1967-03-17
DE19671618583 DE1618583A1 (en) 1965-10-01 1967-03-21 Process for the preparation of aminoalkyl-substituted indanes and tetralines and their acid addition salts
AT278567A AT273947B (en) 1966-03-28 1967-03-23 Process for the preparation of 1-phenyl-1-aminoalkylindanes and tetralines and their acid addition salts
SE04105/67A SE338564B (en) 1966-03-28 1967-03-23
NL6704297A NL6704297A (en) 1966-03-28 1967-03-23
CH435667A CH491076A (en) 1966-03-28 1967-03-28 Process for the preparation of aminoalkyl-substituted indanes or tetralines and their acid addition salts
DK160967AA DK124820B (en) 1966-03-28 1967-03-28 Analogous process for the preparation of aminoalkyl-substituted indanes or tetralins or acid addition salts thereof.
FI670883A FI48458C (en) 1966-03-28 1967-03-28 Process for the preparation of therapeutically valuable aminoalkyl-substituted indanes and tetralins and their acid addition salts.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB03676/66A GB1166711A (en) 1966-03-28 1966-03-28 Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives

Publications (1)

Publication Number Publication Date
GB1166711A true GB1166711A (en) 1969-10-08

Family

ID=10027385

Family Applications (1)

Application Number Title Priority Date Filing Date
GB03676/66A Expired GB1166711A (en) 1965-10-01 1966-03-28 Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives

Country Status (8)

Country Link
AT (1) AT273947B (en)
CH (1) CH491076A (en)
DK (1) DK124820B (en)
FI (1) FI48458C (en)
GB (1) GB1166711A (en)
NL (1) NL6704297A (en)
NO (1) NO127052B (en)
SE (1) SE338564B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002008216A1 (en) * 2000-07-21 2002-01-31 H. Lundbeck A/S Novel compounds and their use as glycine transport inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4662922A (en) * 1984-10-31 1987-05-05 Owens-Corning Fiberglas Corporation Method and apparatus for the production of glass filaments

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002008216A1 (en) * 2000-07-21 2002-01-31 H. Lundbeck A/S Novel compounds and their use as glycine transport inhibitors
US6921774B2 (en) 2000-07-21 2005-07-26 H. Lundbeck A/S Compounds and their use as glycine transport inhibitors
AU2001281740B2 (en) * 2000-07-21 2006-02-16 H. Lundbeck A/S Novel compounds and their use as glycine transport inhibitors

Also Published As

Publication number Publication date
NO127052B (en) 1973-04-30
FI48458C (en) 1974-10-10
AT273947B (en) 1969-08-25
NL6704297A (en) 1967-09-29
SE338564B (en) 1971-09-13
DK124820B (en) 1972-11-27
CH491076A (en) 1970-05-31
FI48458B (en) 1974-07-01

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees